Cephalosporins

Abstract

The syn isomer of a compound of the formula <IMAGE> I in the R or S form or a mixture of R and S forms and their non-toxic, pharmaceutically acceptable acid addition salts wherein the substituents are defined as in the specification having antibacterial activity and their preparation.

What is claimed is: 
     
       1. The syn isomer a quaternary ammonium compound of the formula ##STR74## in the R or S form or a mixture of R and S forms wherein R 1  is selected from the group consisting of ##STR75## R and R' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, ##STR76## Q and Q' are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, X is a single bond or ##STR77## in E or Z form, R b  and R c  are individually selected from the group consisting of an equivalent of alkali metal or alkaline earth metal, magnesium, ammonium and amino or A and A' are the remainder of an easily cleavable ester group or --CO 2  A is --CO 2 .sup.θ and their nontoxic, pharmaceutically acceptable acid addition salts. 
     
     
       2. A compound of claim 1 wherein R 1  is selected from the group consisting of ##STR78## 
     
     
       3. A compound of claim 1 wherein R 1  is selected from the group consisting of ##STR79## 
     
     
        1. 3,4-thiadiazolylthio and methyltetrazolyl. 
     
     
       4. A compound of claim 1 wherein R 1  is ##STR80## 
     
     
       5. A compound of claim 1 selected from the group consisting of (S) (cis) (Z) 5-[[7-[[(2-amino-4-thiazolyl) [carboxy-(3,4-dihydroxy-phenyl) -methoxy]-imino]-acetamido]-2-carboxy-8-oxo -4-thia-1-aza-bicyclo-[4,2,0]-oct-2-en-3-yl]-methyl]-thieno-[2,3-b]-pyridinium in R or S form or in the form of an R,S mixture and in the form of an internal salt or a salt with alkali metals, alkaline-earth metals, magnesium, ammonium hydroxide, amino organic bases, acids and its easy cleavable esters. 
     
     
       6. An antibacterial composition comprising an antibacterially effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier. 
     
     
       7. A composition of claim 6 wherein R 1  is selected from the group consisting of ##STR81## 
     
     
        1. 3,4-thiadiazolylthio and methyltetrazolyl. 
     
     
       8. A composition of claim 7 wherein R 1  is ##STR82## 
     
     
       9. A method of treating bacterial infections in warm-blooded animals comprising administering to warm-blooded animals a bactericidally effective amount of a compound of claim 1. 
     
     
       10. The method of claim 9 wherein R 1  is selected from the group consisting of ##STR83## 
     
     
        1. 3,4-thiadiazolylthio and methyltetrazolyl. 
     
     
       11. The method of claim 9 wherein R 1  is ##STR84##